1-异丁基异喹啉 | 7661-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 1-异丁基异喹啉
• 英文名称: 1-isobutylisoquinoline
• 英文别名: 1-isobutyl-isoquinoline；1-Isobutyl-isochinolin；Isoquinoline, 1-isobutyl-；1-(2-methylpropyl)isoquinoline
• CAS: 7661-40-7
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: ILBZMIKXUUXIHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-异丁基异喹啉 、 碘甲烷 生成 1-isobutyl-2-methyl-isoquinolinium; iodide
  参考文献：
  名称：

  Cannon; Webster, Journal of the American Pharmaceutical Association (1912), 1957, vol. 46, p. 416,417, 418

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-N-(2-苯基乙基)丁酰胺 在 PPA 、 镍 作用下， 生成 1-异丁基异喹啉
  参考文献：
  名称：

  Cannon; Webster, Journal of the American Pharmaceutical Association (1912), 1958, vol. 47, p. 353

  摘要：

  DOI：

文献信息

• Pyridine- and Pyrimidinecarboxamides as CXCR2 Modulators
  申请人：Maeda Dean Y.

  公开号：US20100210593A1

  公开（公告）日：2010-08-19

  There is disclosed pyridine- and pyrimidinecarboxamide compounds useful as pharmaceutical agents, synthesis processes, and pharmaceutical compositions which include pyridine- and pyrimidinecarboxamides compounds. More specifically, there is disclosed a genus of CXCR2 inhibitor compounds that are useful for treating a variety of inflammatory and neoplastic disorders.

  披露了作为药物剂的吡啶和嘧啶羧酰胺化合物，合成过程以及包括吡啶和嘧啶羧酰胺化合物的药物组合物。更具体地，披露了一类CXCR2抑制剂化合物，可用于治疗各种炎症和肿瘤性疾病。
• Alcohols as alkylating agents in heteroarene C–H functionalization
  作者：Jian Jin、David W. C. MacMillan

  DOI：10.1038/nature14885

  日期：2015.9

  The biochemical process of spin-centre shift is used to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors; this represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. A central reaction in DNA biosynthesis is ribonucleotide deoxygenation via the radical-mediated elimination of H2O, which is an example of 'spin-centre shift' (SCS), during which an alcohol C–O bond is cleaved to produce in a carbon-centred radical intermediate. Although SCS is a well-understood biochemical process, it is underutilized by the synthetic organic chemistry community. Here Jian Jin and David MacMillan show that it is possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylations using alcohols as radical precursors. This method represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the merger of photoredox and hydrogen atom transfer catalysis. Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage1. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of ‘spin-centre shift’2, during which an alcohol C–O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides3,4,5,6,7, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.

  利用自旋中心转移的生化过程，通过醇作为自由基前体，可以实现温和的、非传统的烷基化反应。这在合成有机化学领域尚未得到充分应用。本文中Jin Jian和David MacMillan展示了一种方法，即利用这一自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。这种方法首次实现了在广泛应用上将非活化醇作为潜在烷基化试剂，其核心是通过光氧化还原与氢原子转移催化的结合来实现。氧化还原过程和自由基中间体在很多生化过程中都存在，包括脱氧核糖核酸的合成和氧化性DNA损伤。DNA生物合成的关键原理之一就是通过自由基介导的水分子消除反应来脱氧核糖核苷酸，这也是"自旋中心转移"的一个例子。在这个过程中，醇的C-O键断裂，形成碳中心的自由基中间产物。虽然自旋中心转移是一个广为人知的生化过程，但在合成有机化学领域，这一方法尚未得到广泛应用。我们想知道是否有可能利用这个自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。传统的基于自由基的烷基化方法通常需要使用化学计量的氧化剂、提高温度或使用过氧化物，因此一个使用简单且丰富的烷基化试剂的温和协议在合成多样功能化的药物分子上具有很大的应用价值。在这里，我们描述了一种使用醇作为温和烷基化试剂的双催化烷基化杂芳烃的方法。据我们所知，这代表了首次在广泛应用上将非活化醇作为潜在烷基化试剂，其成功在于实现了光氧化还原与氢原子转移催化的结合。该多催化协议的价值已通过药物分子法舒地尔和米力农的后期功能化得到展示。
• Radical C−H Acylation of Nitrogen Heterocycles Induced by an Aerobic Oxidation of Aldehydes
  作者：Subhasis Paul、Manotosh Bhakat、Joyram Guin

  DOI：10.1002/asia.201900857

  日期：2019.9.16

  ketones is described herein. The reaction involves cross-dehydrogenative coupling between aldehydes and heteroaromatic bases with molecular oxygen (O2 ). The key aspect of the method is the generation of reactive acyl radical via homolytic activation of aldehyde C-H bond using O2 as the sole oxidant. The reaction has a good substrate scope with respect to aldehydes and functionalized nitrogen heterocycles

  本文描述了用于合成不对称杂芳基酮的需氧自由基方法。该反应涉及醛和杂芳族碱与分子氧（O2）之间的交叉脱氢偶联。该方法的关键方面是使用O2作为唯一氧化剂，通过醛CH键的均质活化来生成反应性酰基基团。关于醛和官能化的氮杂环，该反应具有良好的底物范围。根据我们的机理研究，建议该反应采用自由基链途径。该方法的合成应用在天然生物碱（±）安格西汀的形式合成中得到了证明。
• General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides
  作者：Bijay Shrestha、Surendra Thapa、Santosh K. Gurung、Ryan A. S. Pike、Ramesh Giri

  DOI：10.1021/acs.joc.5b02077

  日期：2016.2.5

  We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic

  我们报道了有机铝试剂与有机卤化物非常普通的铜催化交叉偶联的第一个例子。进行反应以使烷基铝，芳基铝和炔基铝试剂与芳基和杂芳基卤化物和乙烯基溴化物偶联，从而以良好或优异的收率提供交叉偶联的产物。伯烷基铝试剂和仲烷基铝试剂都可用作有机金属偶联剂。这些反应不会因β-氢化物的消除而复杂化，因此，即使在“无配体”条件下与杂芳基卤化物偶合，也不会用仲烷基铝试剂观察到重排产物。自由基探针的自由基时钟实验和Ph 3的相对反应性研究具有两个不同氧化还原电位的具有两个卤代芳烃1-溴萘和4-氯苄腈的Al表明该反应不涉及作为中间体的游离芳基和自由基阴离子。这些结果与通过使Ph 3 Al与含有p -H，p -Me，p -F和p -CF 3取代基的碘代芳烃反应获得的哈米特图的结果结合在一起，该曲线显示出一条线性曲线（R 2 = 0.99）。 ρ值为+1.06，表明电流转换遵循氧化加减还原途径。
• 6, 11-bridged tricyclic macrolides
  申请人：Or Sun Yat

  公开号：US20070082853A1

  公开（公告）日：2007-04-12

  The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了具有以下结构的化合物I，或其药学上可接受的盐、酯或前药：这些化合物具有抗菌性能。本发明还涉及包括上述化合物的药物组合物，用于治疗需要抗生素治疗的受试者。该发明还涉及通过给受试者施用包含本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。